In the purchase of the Louisiana Territory, then-Secretary of State James Madison and his assistant, James Monroe, connived in making the eastern boundaries of that territory uncertain. They were plotting to eventually use the pretext of unclear boundaries as part of the justification for seizing "the Floridas."

Like with later U.S. covert operations (such as the Spanish-American War, such as the overthrow of Salvador Allende in Chile, such as the Bay of Pigs fiasco, such as the Gulf of Tonkin incident, such as the Persian Gulf War), a similar pattern occurred during President James Madison's Florida intrigues: "a preliminary propaganda phase -- working up excitement in and about the target -- then the organizing of a 'patriot government' opposed to the group we wished to get rid of, then an armed attack by the 'patriots' on the nearest legitimate authority... then an appeal to the United States government to assume control and restore 'order,' a call which the United States government usually answered." From the Florida plot, to the Bay of Pigs and beyond, the basic technique has remained the same.

James Madison, married to the extravagant Dolley Madison (she, 17 years his junior), was as opposite to his wife as night and day. A taciturn, morose man, James Madison may have been sexually impotent, suggests author Joseph Burkholder Smith in his book, The Plot To Steal Florida. Dolley Madison, according to some indications, may have had a history of sexual indiscretions. Madison and his cronies also liked their liquor, often drinking to excess. He also suffered from hemorrhoids and was often accused of "living on laudanum" (an opium derivative).

According to James Madison, the Floridas would sooner or later belong to the U.S. "because their position and the manifest course of events guarantees an early and reasonable acquisition of them." (Emphasis added.) This concept of "manifest course of events" later, in subsequent administrations, became known as "Manifest Destiny."

Instead of a direct invasion of the Floridas, which would have caused diplomatic problems, Madison decided on a more subtle approach. He sent secret agents to the Floridas to stir up a "patriotic movement." These agents offered bribes, principally promises of land, to Americans already living in the region. The "patriots" were to declare independence from Spain and "request support and assistance from the United States."

Chief among the secret agents sent by Madison was the aged Revolutionary War general, George Mathews. General Mathews, "a short old man who spoke with an Irish brogue... and who insisted on wearing one of the three-cornered hats that everyone wore when George Washington was president," was assigned the task of spying on the Spanish government in the area and assessing the chances for the planned coup d'etat.

In December of 1810, "West Florida," an area roughly corresponding to the Florida panhandle, was successfully annexed into the United States, as part of the Territory of Orleans. But "East Florida," the large peninsula jutting out into the oceans, could not be so easily claimed as already included in the Louisiana Purchase. Ponce de Leon had established the Spanish claim to the area in 1521, and large cattle ranches thrived in East Florida. By 1810, East Florida enjoyed increasing prosperity and this led to its being coveted by persons north of its border.

On January 15, 1811, Congress passed an Act "to enable the President of the United States, under certain contingencies, to take possession of [East Florida], and for other purposes." (Emphasis added) "Those last three little words," writes Smith, "were fateful. They gave Madison blank-check authority for covert action." Those last few words, "and for other purposes," bring to mind the National Security Act of 1947 which established the Central Intelligence Agency [CIA]. The CIA was originally meant to function only as a central clearinghouse of intelligence already provided to it by other agencies. Yet the 1947 Act establishing CIA also, incidentally and in passing, allowed CIA to "perform such services of common concern... and such other functions... as the NSC [National Security Council] may from time to time direct." Those last little, "incidental," words, both in the 1811 Act and the 1947 Act, opened up a pandora's box.

General Mathews circulated amongst U.S. citizens already owning property in East Florida, and especially recruited his "patriot army" from settlers in southern Georgia. In return for their assistance, offers of free land were given. Mathews sought to stir up a "rebellion" as pretext for U.S. troops coming in and "restoring order." But British spies by now were aware of what was going on. British minister to Washington William Wyllys wrote a stern letter to James Monroe, charging secret agent Mathews with "corresponding with traitors, and... endeavoring by bribery and every act of seduction to infuse a spirit of rebellion into the subjects of the King of Spain." Since the British were allied with Spain against the French, they did not look kindly on U.S. attempts to grab East Florida. Understand too that Spain was a hugely Catholic country and that the Vatican must have had some interest in the affair. (British spies and Catholic spies later swarmed throughout the south, just prior to the American Civil War.)

In East Florida lived a large colony of escaped slaves. These escaped slaves worked as tenant farmers for the Seminole Indians, who also resided in the region. If East Florida were to be annexed by the United States, both the escaped slaves and the Seminoles feared what would come next.

The upshot is that the "spontaneous rebellion" and consequent hopes of seizing East Florida for the U.S. were thwarted. Part of what derailed the plot was the arrival of The War of 1812, during which British troops burned Washington, D.C. to the ground. President Madison had other worries on his mind, so the grab of East Florida was put aside. Another factor was the resistance put up by escaped black slaves and Seminole Indians: "Bowlegs," half-brother of Chief Payne, went on the warpath. The Spanish Governor helped instigate the Indian uprising by claiming he was unable to deliver his usual gifts to the Seminoles due to "the disruption of the Indian trade" caused by "white invaders." Bands of Indian and black warriors began killing the "white invaders." Fearing for the safety of their families, the "patriot army" shouldered their muskets and headed north to protect their homes.